Embedded in self-determination theory (SDT), the purpose of this study was to explore the coaching in a soccer program aimed at promoting life skills to disadvantaged youth. Non-participant observation and video footage of the coaching styles and behaviors, combined with interviews with program participants, revealed that some autonomy-supportive strategies may be difficult to employ and potentially counterproductive in some circumstances. Furthermore, coaches who were interpersonally involved with participants were able to offset some negative consequences of controlling behaviors. This study gives new insight into the complex relationships that exist between SDT-based coaching behaviors, positive youth development, and the soccer context.